


Two Souls, One Heart

by anc



Series: NSFW OTP 30 Day Challenge [1]
Category: Supernatural
Genre: 69 (Sex Position), Anal Sex, Blow Jobs, Cowboy!Dean, Dirty Talk, Doggy Style, Explicit Language, Facials, First Time, Fluff, Hair-pulling, I mean I like a flagrant disregard for condoms, Lawyer Castiel, Light Bondage, Light Dom/sub, M/M, Masturbation, Name-Calling, Secretary Dean, Skype Sex, Smut, Soldier!Dean, Spanking, Student!Dean, Switching, Unsafe Sex, teacher!Castiel
Language: English
Status: In-Progress
Published: 2014-11-16
Updated: 2014-12-09
Packaged: 2018-02-25 13:44:10
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 14
Words: 17,481
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2623898
Author URL: https://archiveofourown.org/users/anc/pseuds/anc
Summary: <blockquote class="userstuff">
      <p>Prompt: 1. Cuddles (naked)</p>
    </blockquote>





	1. Chapter 1

**Author's Note:**

> Prompt: 1. Cuddles (naked)

It was the middle of the night when Dean found himself being jarred awake by the feeling of Castiel trembling beside him. Cracking open his left eye, he looked over at his blue eyed lover to see that somehow, he was without covers. The blanket that had been over their naked bodies when they had fallen asleep was MIA and Dean was almost positive that he was to blame for its absence. 

Sitting up slightly, he scanned the floor on his side of the bed, noticing instantly that the large blue blanket in question was in a heap on the carpet. 

In his defense, Dean was not accustomed to sleeping under a blanket. Sure, he would use one during the winter but more often than not, a sheet was all he needed. And the ONLY reason he had been using a blanket that night was for the benefit of his boyfriend Castiel, who sadly enough, got cold at the drop of a hat. Not that his willingness to compromise did Castiel much good though. Half the time Dean would end up throwing the blanket off them unintentionally in his sleep, resulting in his boyfriend having to practically crawl underneath him to avoid hypothermia. And it seemed that tonight was one of those nights. 

"Son of a bitch," Dean whispered in frustration, trying to shake himself out of his sleepy daze as he reached out slowly with his right hand, grabbing the blanket so that he could toss it back over the two of them. 

Once he had successfully recovered his lover and himself, Dean turned onto his left side, wrapping his arm securely around Castiel's middle. Then, pressing his chest to the blue eyed man's back, he nuzzled up close to his boyfriend in an attempt to get him warm.

"Th-thanks baby," Castiel stuttered suddenly, revealing that he was awake. 

His teeth were chattering due to how cold he was and the sound of his trembling voice only made Dean hug him tighter.

"No problem, Cas. Can't have you turning into a popsicle, now can we?" Dean chuckled in response. 

"Well, it's a good thing that you covered me up when you did. 'Cause I was about two seconds away from being branded with a Ben and Jerry's label," Castiel joked, relaxing against his boyfriend's warm skin. 

"Mm, Cas flavored ice cream. I could dig that," Dean said huskily, placing a tender kiss to Castiel's neck.

"Shut up and go back to sleep, dork," Castiel scolded playfully as he closed his eyes.

"Night Cas. I love you," Dean yawned, cuddling even closer to the blue eyed man.

"Good night...I love you too, baby," Castiel mumbled affectionately before drifting back to sleep.


	2. Chapter 2

**Notes for the Chapter:**

> Prompt: 2. Kiss (naked)

"Son of a bitch," Dean whined, accidentally applying a little too much pressure to the very large purple bruise on his left side near his ribs when he was trying to rinse the soap off his body. 

Looking down, he examined the injury with care, making sure the sensitive skin was not distended or torn. He knew with certainty that the bruise was not anything that needed medical attention, but due to its size and location it was proving to be a nuisance. 

Not that Dean was really complaining. By that point in his life he was disturbingly used to being in pain and felt like he had gone 12 rounds with a brick more often than he felt healthy. And it was not uncommon for Dean to have such an injury like the one he did currently. As a professional bull rider and a member of the Professional Rodeo Cowboys Association, he was accustomed to his body being constantly littered with contusions and cuts. It was a product of the sport, and if Dean was being completely honest, he was damn proud of his massive bruise. He had earned it in the face of adversity during a competition, and that fact, filled him with pride. 

The bull he'd drawn that night had been rowdy, definitely living up to his reputation of being "unridable." And when he had sat down on the animal's back, it had put up quite the fight, bucking Dean against the gate before the buzzer even sounded. It was then that he had sustained his injury and as a result, had to ride hurt. However, that didn't stop Dean from getting his eight second ride and putting on one hell of a show for the judges. 

In the end, he had scored a whopping 90 points out of 100, earning him the first place buckle and price money. And that was why, regardless of how bad his side was throbbing, he had no regrets. Dean would have gladly taking his current bruise and countless others if it meant being the champ. 

Smirking cockily at the memory of his name being announced in victory, Dean turn around slowly, positioning himself in front of the shower head so that the hot water cascaded over his sore back muscles. Letting out a small sigh, he had just closed his eyes when he heard the shower curtain being drawn back. 

Re-opening his green orbs, Dean chuckled softly when he saw his boyfriend Castiel, stepping into the tub with him. 

Smiling over at the other man, Dean couldn't stop himself from giving his boyfriend a thorough once over as he licked his lips hungrily, the sight of Castiel's gorgeous naked body making his dick stand at attention. 

"Hey baby," Dean purred, reaching forward to grab Castiel by the hips. 

"How are you doin', babe? Is the hot water helpin' at all with the pain?" Castiel asked worriedly, wrapping his arms around his boyfriend's neck. 

"I'm okay, Cas, promise. You know it's going to take a lot more than a little 'ol 1,500 pound bull to put your man out of commission," Dean replied sheepishly, leaning forward to press his lips against the other man's.

Opening his mouth to give Dean better access, Castiel returned the kiss, moaning softly as his boyfriend's hands found his ass, giving it tight squeeze. 

"Whoa, easy there cowboy," Castiel mumbled against Dean's lips when he felt him rock his hips forward, brushing his erection against the shorter man's stomach. "You need to be doing a little less romancing and a lot more showering. The sooner you are done, the sooner you can take some ibuprofen and get some rest," he added, running his fingers through Dean's wet hair.

"Hey, I just won first place at the rodeo, baby. I want to celebrate, not sleep," Dean retorted. 

"Well how about this? If you move your ass, you can celebrate by giving me a repeat performance of your ride from earlier. Of course, I'll be extremely disappointed if it doesn't last longer than eight seconds," Castiel teased, letting out a small, needy whimper when Dean slapped him on his left ass cheek playfully. 

"Trust me, baby. When I get you in our bed, I'm gonna give you my best ride yet. And I'll prove that this cowboy can hold his own way passed the buzzer," Dean joked back, grinning at his boyfriend slyly. 

"Looking forward to it, babe," Castiel replied, shooting Dean a smile in return before picking up the shampoo to assist his boyfriend with washing his hair.


	3. Chapter 3

**Notes for the Chapter:**

> Prompt: 3. First Time

"Are you nervous, my love?" Castiel asked softly, shooting Dean a sympathetic look.

They were both naked and on Castiel’s bed, Dean lying on his back with his bowed legs spread wide, his beautiful blue eyed lover positioned on his knees between them. But even though Dean’s cock was fully hard and dripping pre-cum at the sight of Castiel’s pale, muscular body displayed in front of him, he was also visibly terrified. 

"Understatement of the century, darlin'," Dean retorted, his whole body tensing when he saw Castiel pop open the cap on the bottle of lube that was in his left hand.

This was the first time they had ever attempted to have sex together and needless to say, Dean was freaking the fuck out. In all honesty, if Dean hadn't been so petrified due to his current situation, he would have probably laughed at himself for being so damn nervous. It was ridiculous!

After all, it had been Castiel's decision for them to wait to have sex in the first place. For his boyfriend, losing their virginity to each other was a huge deal and because of that, Dean had agreed to abstain from sex until Castiel was ready out of respect for him. But as for Dean personally, waiting, not waiting, it didn’t really make a difference. 

While Castiel held the act of sex in high regards, believing it was something beautiful and soul melding, for Dean, his thoughts weren’t that deep. Up until that moment, sex had just been something he wanted to have because it was supposed to feel good. And when they had first started dating, Dean hadn’t had any fantasies about sex being magical or serving as a way to bring Castiel and him closer together.

However, four years later in their relationship when the moment of truth had finally arrived, it was surprisingly Dean, not Castiel, that was sweating bullets. This was due largely to the fact that he wanted Castiel's first time to be something worth remembering and for him to be able to cherish the thought of it. He didn’t care if the experience was good for him; he just wanted to please Castiel. And that pressure, even though it was completely unwarranted, was stressing Dean out.

 

"It's okay, Dean. I've got you. I'm going to make you feel so good," Castiel purred before cautiously reaching between Dean's open legs, massaging his balls with his warm, wet fingers. “Just try to relax,” he added, making his boyfriend roll his eyes despite the that all of his nerve ending were on fire.

“How am I supposed to relax when a sexy son of a bitch like yourself has his hand on my junk?” Dean asked sassily.

Instead of responding verbal however, Castiel took that opportunity to move his hand down a little farther, gently pushing his index finger inside of Dean.

" _Jesus_!" Dean moaned loudly a few seconds later when his boyfriend found his prostrate.

"No, I'm Castiel," his blue eyed lover teased as he began to work him open.

"Sarcastic little shit," Dean chuckled breathlessly, throwing his head back against his pillow in ecstasy when he felt Castiel drag his finger over the sensitive bundle of nerves inside him. 

"You love it," Castiel shot back, adding a second finger.

"Guilty...oh _fuck_ ," Dean whimpered, thrusting his hips upward as his boyfriend continued to hit his sweet spot. 

"...Jesus Christ, Dean. You have no idea what you’re doing to me right now. You look so fucking good stretch out around my fingers like this," Castiel said, his voice completely wrecked. 

"Cas, please," Dean mewled, gripping the sheets beneath him tightly. 

"Shh baby, I'll give what you want. I just need to prep you a little more, don't wanna hurt you," Castiel explained, carefully adding a third digit to Dean's hole.

"I know, sweetheart. I just want you so bad," Dean gritted out, miraculously having the where-with-all to shoot his boyfriend a sly little wink.

"I want you too, Dean, so much. I love you," Castiel told him, finally removing his fingers which made his boyfriend whimper at the loss.

"I love you too, Cas," Dean replied, pulling Castiel forward for a quick kiss.

“You ready?” Castiel asked huskily, his breath hot against Dean’s lips.

“I was ready like…yesterday,” Dean teased as Castiel sat back on his heels, it being his turn to roll his eyes at his boyfriend’s comment. 

Then, while Castiel grabbed the bottle lube once more to slick himself up, Dean reached down to stroke his own cock, proving that he wasn’t kidding about being ready. By that point, he was so blinded by lust that he could barely function. 

"Easy baby, or it will be over for you before we even get started," Castiel laughed, scooting forward to wrap Dean's legs around his waist.

"C'mon Cas, I'm dying here," Dean pleaded as he reluctantly removed his hand from his cock.

"You want me that bad, baby?" Castiel taunted, lining himself up with Dean's entrance, circling the head of his cock teasingly around the tight ring of muscle. 

"Get inside me now, you fucker," Dean ordered, gasping when Castiel complied, pushing into him slowly. 

"Better?" Castiel inquired as he bottomed out, unable to suppress a shiver of pleasure that rolled through his body. 

"Y-yes," Dean moaned.

The feeling of Castiel inside him was slightly strange at first, a dull, aching sensation flooding his senses. However, the more time his boyfriend gave him to adjust, the more awesome Dean began to feel as he relaxed his muscles and focused on Castiel's hands which were softly caressing his thighs. 

"Do you want me to move?" Castiel whispered after a short moment of silence, his voice gentle but a little strained. 

"Yeah baby, come on," Dean urged, reaching up to wrap his arms around Castiel's neck when the blue eyed boy leaned forward, pressing their bodies together. 

Doing as he was told, Castiel then began to roll his hips upward slowly and sensually, making sure to hit Dean's prostate with each thrust.

"Fuck Dean, you're still so tight. Feels so fucking good," Castiel purred, moaning softly when Dean leaned up in order to pulled him into a sloppy, open mouth kiss. 

"Harder baby, please," Dean begged, biting Castiel's bottom lip.

Putting more force behind his thrusts, Castiel continued to kiss Dean, licking and sucking at his swollen, pouty lips. 

"Like that, babe?" Castiel asked, purposely slamming into Dean hard enough to make him cry out. 

"Fuck! Yes, just like that Cas," Dean groaned, his fingers digging into the tops of Castiel's shoulders, bruising his skin.

Smirking at Dean's reaction, Castiel slowly trailed his right hand down the front of his boyfriend's body before wrapping it around his cock. He then began to pump his wrist lazily, the steady pace driving Dean insane as he let out a needy whimper. 

“You’re close, aren’t you gorgeous?” Castiel asked seductively. 

“Yes, oh fuck,” Dean gasped when his boyfriend tightened his grip on his cock, stroking him a little bit faster.

“Then let go baby, cum for me,” Castiel coaxed, the molten hot sound of his voice exactly what Dean needed to hear to send him over the edge. 

“Oh God, Cas!” Dean shouted, his stomach muscles clenching as an orgasm ripped through his body. 

“That’s it, Dean. So good for me,” Castiel praised, continuing to stroke him through his release until he was too sensitive to take any more. 

“Fuck, that was amazing,” Dean breathed out, moaning like a pornstar when he saw Castiel lick some of his cum off his hand.

"I'm glad you enjoyed it, gorgeous," Castiel replied, stilling his hips for the moment as he looked down at his boyfriend lovingly. 

“You’re turn baby,” Dean stated, reaching up to thread his fingers through the blue eyed boy’s hair. 

Beginning to thrust his hips once more, Castiel pressed his palms flat against Dean’s chest, making soft, needy sounds as the boy beneath him began to move his hips as well. 

“Dean, I love you so much. I’m beyond thankful that you are the man I’m sharing my first time with,” Castiel whispered, pulling Dean into another passionate kiss. 

“I love you too, Cas. I feel the same way,” Dean agreed as he continued to grind down onto his boyfriend’s cock. 

Soon, Castiel's movements started to become sporadic and it wasn't long before he too found his release, throwing back his head as he felt a wave of pleasure wash over him.

“Holy fuck, Dean!” Castiel yelled, a warm, tingling sensation spreading throughout his body. 

“Damn Cas, you look so fucking beautiful when you cum,” Dean told him, placing a tender kiss to his boyfriend's forehead when he collapsed on top of him.

Breathing heavily, Castiel didn't bother to roll off of Dean as the two of them laid there, soaking up the afterglow effects of their orgasms.

“Well, I guess that means I’ll just have to do it again. You know, so you can enjoy the scenery,” Castiel replied after a moment, peppering Dean’s chest with kisses. 

“I have absolutely no objection to that,” Dean joked back, wrapping his arms tightly around the man who had stolen his heart.


	4. Chapter 4

**Notes for the Chapter:**

> Prompt: 4. Masturbation

Castiel was lonely.

 

With his boyfriend being a Special Forces officer in the United States Army, he often spent months on end by himself while Dean was off on some covert mission. And it sucked. It epically sucked not being able kiss or touch, or even talk to his boyfriend on a regular basis. Instead of taking long romantic walks or cuddling up in bed together like a normal couple, Dean and Castiel’s private time consisted of random, often monitored, long distance phone calls that never lasted more than ten minutes. They had been together for seven years, Dean spending the last five of them constantly traveling back and forth from Kansas to Iraq and needless to say, Castiel missed him terribly. All he wanted was for Dean to stay with him, and the thought of his boyfriend walking out their front door and possibly never coming back ripped him to shreds.

 

But most of all, it killed Castiel that he was selfish enough to wish that Dean would give up his job as a sniper for good. He knew that made him a horrible person, especially considering the fact that his boyfriend was responsible for saving thousands of lives by taking out known terrorists in several different foreign countries. However, he couldn't, and would not apologize for wanting Dean to be safe and by his side rather than countless miles away in enemy territory where he was ALWAYS in danger.

 

And if Castiel was being truthful, his boyfriend's safety wasn’t the only thing he longed for. He also wanted, more than anything, to feel the tenderness of Dean's touch again. It had been almost five months since they had been intimate with each other and Castiel was starved for affection. And on that particular night, he was so desperate and so horny that he would have sold his soul to be in Dean’s arms.

 

But unfortunately, he knew that wasn’t plausible. Which was why Castiel had decided to take matters into his own hands, doing what needed to be done to satisfy his lust before it consumed him.

 

 

 

_OoOoO_

 

 

 

Getting completely naked, Castiel laid himself out on Dean’s side of their large, four-poster bed, relaxing against the warm mattress as he let out a deep, calming breath. Once he was comfortable, he then spread his legs open, reaching down with his lube soaked right hand to stroke his cock slowly.

 

Sliding his hand upward, Castiel teased himself, swirling his thumb around the head of his cock, smearing the small bead of pre-cum that was pooled at the top.

 

" _Mm, oh God_ ," Castiel breathed out, slipping his free hand, which was also slick with lubricant, between his legs to gently push a finger inside himself.

 

 He then started to thrust the single digit in and out of his tight, puckered hole, gasping loudly when he found his prostate. As he continued to move his right hand around his cock, Castiel massaged the little bundle of nerves inside himself, raising his hips up off the bed, the pleasure he was feeling causing him to make loud, animalistic sounds.

 

With his eyes closed tightly, Castiel focused on the image of Dean, picturing his flawless tanned skin littered with freckles and his gorgeous green eyes shining with happiness as a devilish little smirk tugged at the corner of his pouty lips.

 

"Ho-holy shit, _Dean_ ," Castiel moaned, pretending it was his boyfriend's hands, not his own, that were bringing him closer and closer to his release.

 

"Oh fuck, Dean!" he yelled, flicking his wrist one last time before a white-hot sensation shot through his body.

 

Feeling his muscles clench, Castiel arched his hips high off the mattress, coming hard. Long, hot ropes of cum spurted all over his hand and stomach as he worked himself through his orgasm, not stopping until he was boneless and panting.

 

"Damn Winchester. Even when you aren't here, you still rock my world," Castiel chuckled breathlessly before gently removing the finger he had inside him.

 

Then, closing his eyes once more, Castiel decided to stay put for a moment, attempting to regulate his breathing.

 

It wasn't until about fifteen minutes later that he finally got up from the bed, his legs a little wobbly, to make his way to the bathroom.

 

Once he reached his destination, he quickly turned on the shower, letting the water warm up a bit before stepping into the tub. Standing under the soothing spray, Castiel let out a long, sad sigh, his mind filled with nothing but the thought of his beautiful green eyed solider.

 

'Three more months," he thought, trying desperately to be optimistic. 'In three short months Dean will be home and I will have him all to myself.'

 

Smirking, he couldn't help but let his mind wander at the thought of Dean's return, thinking of all the things he was going to do to his boyfriend when he finally got him in their bed again.


	5. Chapter 5

**Notes for the Chapter:**

> Prompt: 5. Blow Job

“Baby, stop. We’re going to be late for work,” Castiel whined, reluctantly letting Dean removed the towel that was wrapped around his waist. 

Castiel had just gotten out of the shower and was making his way across their bedroom to the closet to grab his work clothes when his boyfriend had blocked his path. 

“C’mon Cas, we’ve got plenty of time,” Dean replied, seductively running his hands up Castiel’s bare sides as he placed chased kisses to his neck. 

“You’re only saying that because you’re already dressed, asshole,” Castiel shot back, curling his fingers around Dean’s biceps when the green eyed man nipped at his jugular before starting to suck at the sensitive skin.

“Do you really want me to stop, sweetheart?” Dean asked huskily, trailing kisses down Castiel’s chest. 

“You know I don’t,” Castiel breathed out, a sharp gasp escaping his lips when Dean’s tongue flicked across his right nipple. 

Sliding his strong, callused hands down the front of Castiel’s body, Dean swirled his tongue around the colored tissue, making his boyfriend moan loudly. 

“That’s right, Cas. Don’t hold back, I wanna hear you,” Dean purred, nipping at his chest before sinking to his knees in front of Castiel, peppering small kisses all over his stomach. 

“ _Dean_ ,” Castiel whispered desperately when he felt his boyfriend’s hands on his thighs, caressing the smooth flesh. 

“You love it when I touch you like this, don’t you baby?” Dean asked, kissing his way down Castiel’s stomach to the top of his right thigh. 

“Yes, Dean please,” Castiel mewled, his cock beginning to harden. 

“Be patience, Cas,” Dean chuckled, lowering his lips to the inside of Castiel’s leg. 

“Oh God,” Castiel groaned when he felt Dean begin to lick and suck at the sensitive flesh. 

Threading his fingers into Dean’s hair, Castiel closed his eyes, trying to control his breathing as his boyfriend teased him. 

“Do you like it when I kiss you here, Cas?” Dean inquired, leaning over to place a hot, wet kiss to the inner part of Castiel’s left thigh. 

When switching his attention from Castiel’s right thigh to his left, Dean was careful not to come in contact with his boyfriend’s cock, which was now heavy and dripping with pre-cum and the deliberate action made Castiel groan in frustration. 

“Yes, but right about now I’d like you to put your mouth somewhere else,” Castiel growled, a shiver of pleasure rolling through his body when Dean lightly trailed his fingertips up the outer part of his thighs, not stopping until he reached his hips. 

“And where would that be, baby?” Dean taunted as he looked up into Castiel’s bright blue eyes which were hooded with lust. 

“Dean, _please_. I need to feel those gorgeous lips of yours around my cock,” Castiel begged, tightening his hold on Dean’s hair. 

“You mean something like this?” Dean asked sheepishly before leaning forward to gently kiss the tip of his boyfriend’s erection.

“ _Dean_ ,” Castiel whined in response. “Quit messing around.”

“What? Was that not what you wanted? Maybe you want something more like this,” Dean mused, moving his mouth a little farther back to lick the base of Castiel’s cock. 

“Ho-holy fuck,” Castiel moaned, pulling Dean’s hair roughly. 

Smirking, Dean repeated the action; wrapping his left hand around his boyfriend’s cock to stroke it slowly. Setting a steady pace, he then leaned down to run his tongue over Castiel’s balls, making him shout out in pleasure. 

“Well, baby? Is this what you wanted?” Dean questioned after a moment, licking up the length of his boyfriend’s erection before swirling his tongue around the slit, lapping at the pre-cum oozing from it. 

“Yes Dean, just please don’t stop,” Castiel pleaded, cursing under his breath when Dean finally took him into his mouth. 

Moving his lips upward at an agonizingly slow pace, Dean made sure to use as much saliva as he could to get his boyfriend nice and wet while he massaged his tongue against Castiel’s erection. 

“That’s it, Dean…So good,” Castiel praised, tugging at his lover’s hair when he began to bob his head, making Dean moan around his cock. 

Raising up his right hand, Dean wrapped his fingers loosely around his boyfriend’s hard-on, stroking him teasingly while continuing to use his mouth. 

“Cas,” Dean moaned suddenly, pulling back to look up at the handsome blue eyed boy standing in front of him. “You wanna fuck my mouth?” he asked, grinning like the Cheshire cat when Castiel visibly shuddered, whimpering in need. 

“ _YES_ ,” Castiel replied, sounding far more desperate than he had meant to. 

In response, Dean slid his lips down Castiel’s length once more, bobbing his head a couple of times before allowing the blue eyed boy to rock his hips forward, fucking into his mouth. 

“Fuck baby, that feels so damn good,” Castiel moaned, holding Dean’s head in place as he pushed into his mouth farther, his boyfriend relaxing his throat so he could take more. 

Humming in response, Dean ran his hands up Castiel’s thighs before snaking them around his body to grab both his ass cheeks, massaging the meaty flesh with his fingertips. 

“Oh… _fuck, I’m so close Dean_ ,” Castiel breathed out, feeling a warm sensation pooling in the pit of his stomach. 

Swirling his tongue against the shaft of Castiel cock one last time, Dean then removed his mouth from his boyfriend’s erection completely before staring up at him, his eyes gleaming with mischief. 

“Where do ya wanna cum, baby?” Dean asked, his voice completely wreck. “On my face? You’d love that, wouldn’t you?” he added as he began to stroke Castiel lazily with his right hand. 

“Yes, yes, please,” Castiel whimpered. 

Upon hearing his boyfriend’s confirmation, Dean began to pump his fist faster, reaching up with his free hand to massage Castiel’s balls, working him toward his release. 

“C’mon baby, cum for me,” Dean coaxed. 

Complying with boyfriend’s wishes, Castiel felt his stomach muscles clench as an orgasm washed over his body. Shouting out Dean’s name, Castiel watched through hooded eyelids as his boyfriend continued to stroke his cock until long, hot ropes of cum splashed across his lips and chin. 

“ _Damn_ ,” Castiel whispered, his whole body tingling as he gently removed his fingers from Dean’s hair. 

“You good Cas?” Dean questioned, grinning when his boyfriend moaned at the sight of him licking the cum off his lips. 

“I’m excellent,” Castiel chuckled as he helped Dean to his feet. “But I’m pretty sure that filthy mouth of yours is going to be the death of me…Oh, and it’s also made me thirty minutes late for work.”

“Quit your bitching,” Dean teased, wrapping his arms around the blue eyed boy’s waist. “If there was ever a good excuse for being late, getting head would be it.”

“I can’t argue with that,” Castiel replied, kissing the tip of Dean’s nose before seductively dropping to his knees.

“What cha doin’, baby?” Dean asked playfully as Castiel unbuckled his belt. 

“Hey, we’re already late. Might as well take a little extra time to return the favor,” Castiel explained, shooting his boyfriend a sly wink.


	6. Chapter 6

**Notes for the Chapter:**

> Prompt: 6. Clothed Getting Off

Dean was bored as hell.

 

It was early Monday morning and he was stuck in English class, forced to listen to some monotonous lecture about the novel To Kill A Mockingbird. It was bullshit! Dean could have been catching up on his shut eye but no, he had to be sitting at his uncomfortable ass desk, listening to his lame ass teacher going on and on about Atticus Finch. To be honest, Dean was pretty sure his teacher had a hard-on for the guy, fictional or not.

 

But at least Dean had one saving grace, the delicious eye candy standing straight in front of him. ‘Cause despite his teacher’s dull choice of subject matter, the guy was smokin’ hot. While most of the teachers at the private school of Lawrenceville Academy were ancient and sixes at best, Castiel Novak was a solid ten. But it wasn’t just Mr. Novak’s looks that got Dean all hot and bothered. Sure, his teacher’s flawless tanned skin, messy black hair, and bright blue eyes were all grade A boner material, but there was also something about the way the man carried himself that had Dean drooling all over his desk half the time. And don’t forget that voice. Mr. Novak had a set of vocal cords that were blessed by the gods themselves and every time he opened his mouth Dean swore that he could hear angels singing.

 

“Hey, Dean.”

 

The sound of someone whispering to him jarred Dean back to reality and he quickly pulled himself away from his inappropriate thoughts to realize that Lisa, the girl sitting at the desk next to him, was trying to get his attention.

 

“Yeah Lis?” Dean asked, leaning closer to her in hopes that Mr. Novak, who was currently writing on the chalkboard and therefore had his back to the class, wouldn’t hear them.

 

“Wanna come to Molly’s party with me on Saturday?” Lisa inquired, smiling at him sweetly.

 

However, before Dean could tell her ‘hell yeah,’ Mr. Novak caught them talking.

 

“Mr. Winchester,” Mr. Novak scolded, folding his arms across his chest.

 

“Yes sir?” Dean responded innocently.

 

“How many times have I reprimanded you for talking in class?” Mr. Novak questioned.

 

“Honestly sir? I’ve lost track,” Dean confessed, causing some of his fellow classmates to giggle.

 

“You just earned yourself detention, Mr. Winchester. I’ll see you after school,” Mr. Novak informed him before going back to his lecture like nothing happened.

 

Sighing dramatically, Dean slumped forward to put his head on his desk. He already had detention, so he figured it wouldn’t hurt to get some shut eye.

 

 

 

 

 

 

**_OoOo_ **

 

 

 

 

“Mr. Winchester, please come in and sit down,” Mr. Novak said politely as Dean walked into the empty class room.

 

“Thanks…” Dean mumbled, heading over to his teacher’s desk to stand in front of it.

 

“I’m only going to keep you for an hour, Mr. Winchester. Don’t look so depressed,” Mr. Novak teased, giving him a small smile.

 

Blushing, Dean dropped his gaze to the floor, embarrassed that his teacher had not only caught him gawking at him, but had mistaken it as pouting.

 

“Oh, sorry…It’s not…I was just thinking…” Dean said, fidgeting nervously.

 

“Something on your mind, Mr.- …Dean?” Mr. Novak asked, making Dean look at him with wide eyes.

 

“...Nah, nothing in particular…I was honestly just thinking about how damn good looking you are,” Dean blurred out.

 

“Mr. Winchester that was a highly inappropriate statement…” Mr. Novak stuttered, an expression of exasperation on his face as he reached up to loosen the blue tie around his neck.

 

The older man looked visibly uncomfortable, but Dean wasn’t sure if it was because he truly thought he was being inappropriate or because he was ashamed that he didn’t.

 

“Why Cas? ‘Cause of our age difference? I’m legal dude, you’re all good,” Dean joked, dropping his innocent act as he slid his backpack off his shoulder to sit it on the floor before sauntering around Mr. Novak’s desk to stand next to him.

 

“You’re my student, Dean. It’s not right,” Castiel said sternly, trying his best to look authoritative as Dean ran his fingers through his messy black hair.

 

“I don’t remember you protesting this much the last time I came onto you...If my memory serves me correctly, you were practically begging for me to bend you over,” Dean mused, leaning down to nip at his teacher’s right earlobe.

 

Wincing at the mention of their previous transgression, Castiel gently pushed the younger boy away, making him let out a pouty little whine as the older man stood up from his chair.

 

“…That was a mistake...” Castiel gritted out, gasping in surprise when Dean grabbed him by both shoulders and pushed him back against the chalkboard.

 

“The fact that your dick is rock fucking solid says otherwise, baby,” Dean taunted, pressing their bodies together as he palmed at the older man’s erection with his right hand.

 

“ _Dean_ ,” Castiel moaned, his eyes rolling back in ecstasy.

 

“That’s better, Cas,” Dean said seductively before leaning forward to pepper kisses all over his face.

 

“Oh, fuck…M-move a little faster, please,” Castiel begged, thrusting himself against Dean’s hand.

 

“Damn baby, you that desperate to get off? You gonna cum in your pants for me like the needy slut that you are?” Dean asked, slowly running his hand down the front of the older man’s crotch, causing him to moan loudly.

 

“Yes, Dean _please_!” the blue eyed man mewled, wrapping his hands around Dean’s biceps as he continued to buck his hips.

 

“Quiet angel, you don’t want anyone to hear us, do you?” Dean questioned sheepishly before capturing the older man’s mouth with his own, licking and sucking at his soft, pink lips.

 

Whimpering into the kiss, Castiel held onto his student's arms tightly as he felt his stomach muscles clench, a warm, euphoric feeling consuming him.

 

“ _Fuck_ ,” Castiel growled, arching his back as Dean worked him through his orgasm.

 

“That was fucking hot,” Dean whispered when Castiel slumped against him, the older man still holding onto him for support.

 

“…Damn it, Dean...What are you doing to me?” Castiel asked, his chest heaving.

 

“Anything you want, baby,” Dean teased.

 

“This is serious! I’ve never done anything this reckless in my life…” Castiel huffed, finally looking up at Dean.

 

“Just face it, Cas, you can’t resist me,” Dean chuckled as he shot the older man a sly wink.

 

“So it seems,” Castiel replied, his voice dripping with agitation. “…No matter. I have my ways of getting even with you for leading me into temptation. Take a seat, Mr. Winchester.”

 

“But Cas,” Dean whined, his dick throbbing in his jeans.

 

“This is detention, Mr. Winchester. You are being punished, not rewarded. Now, sit down and do your homework,” Castiel ordered.

 

“You’re a bastard,” Dean grumbled, shoving the older man in the chest before he stomped over to a desk and sat down.

 

“…Pout all you want Mr. Winchester…We both know you love it,” Castiel taunted, carefully walking over to his chair, trying to ignore the gross, sticky feeling in his pants.

 

“Shut up,” Dean deadpanned, scowling when Castiel burst out laughing.

 


	7. Chapter 7

**Notes for the Chapter:**

> Prompt: 7. Dressed/naked (half dressed)
> 
> ...I think this follows the prompt...Haha Oh, and sorry I'm posting this so late. Homework...SO much homework. Lol 
> 
> Anyway, enjoy!

“Dean?” Castiel panted from his position on his back, lying in front of his lover completely naked with his legs spread open. 

“Yeah Cas?” Dean answered, pumping his lube soaked fingers in and out of Castiel’s tight hole. 

“Could you…ah fuck…do you think you could put your leather jacket back on? Want you to wear it while you fuck me,” Castiel said, arching his hips off the mattress when Dean’s fingers hit his prostate. 

“You kinky little bastard,” Dean teased, slowly removing his fingers, making Castiel whimper. 

“I just really like the way it looks on you…And I think it would look even better on you while you're fucking me,” Castiel purred, smirking when Dean was unable to hold back a needy moan. 

“Damn, okay gorgeous. You win,” Dean told him, quickly leaning over to grab his leather jacket that he had discarded on the floor next to the bed. 

Once he retrieved the article of clothing, Dean threw it over his shoulders, pulling on the jacket so that it was the only thing covering his otherwise naked body. 

“This what you want, Cas?” Dean questioned, flashing him a bright smile as Castiel eyed him lustfully. 

“Close,” Castiel teased, reaching up to pull Dean on top of him, using the jacket as leverage. “It’d be exactly what I wanted if you were inside me.”

“Well,” Dean said, slipping his right hand between their bodies to wrap it around his erection. “You know I can’t deny you anything. I’ll always give you what you want,” he added, lining himself up with Castiel’s hole before pushing into him agonizingly slow, making the man beneath him scream his name. 

“That’s it babe, that’s exactly what I want,” Castiel groaned, his hands gripping at Dean’s leather jacket tightly as he felt his lover begin to thrust his hips. 

With a cocky smirk on his face, Dean leaned down to kiss Castiel’s neck, picking up the pace of his movements.

“Does this really turn you on baby? Me fucking you like this,” Dean whispered as he wrapped his hand around Castiel’s throbbing cock before starting to pump his fist lazily. 

“Oh God, yes,” Castiel mewled, rolling his body upward, working desperately to reach his release. 

“Fuck, Cas,” Dean moaned, feeling a warm sensation pooling in the pit of his stomach. 

“Dean, faster please,” Castiel begged, reaching down to wrap his hand around the one Dean had on his cock, stroking himself with his lover. 

“C’mon baby, let go,” Dean coaxed, watching as Castiel threw his head back against his pillow, moaning loudly as he came, splashing long, hot ropes of cum all over Dean’s stomach. 

“Holy fuck,” Castiel breathed out, biting his bottom lip as Dean pumped into him a couple more times before finding his release as well. 

“Damn Cas,” Dean groaned, collapsing on top of his lover after he worked himself through his orgasm. 

Finally releasing his hold on Dean’s jacket, Castiel reached up to run his fingers through Dean's hair as he tried to regulate his breathing. 

“You should fuck me like that more often,” Castiel told him sheepishly, smiling down at his lover. 

“I’ll fuck you any way you want me to, baby,” Dean replied without hesitation, making Castiel chuckle.


	8. Chapter 8

**Notes for the Chapter:**

> Prompt: 8. Skype sex
> 
> ...I swear I live in a hole and have used Skype like once in my life...I apologize if this sucks! Lol

Moaning loudly, Castiel leaned back against the couch in his hotel room; his legs spread open toward the camera on his laptop as he slowly pumped his vibrator, which was slick with lube, in and out of his tight, puckered hole. 

“Fuck baby, I wish I was there. Wish you were fucking yourself on my cock and not a toy,” Castiel heard Dean say over their Skype call, his voice sounding completely wrecked.

“Oh God, me too Dean,” Castiel mewled, his blood turning molten in his veins when he drug the vibrator over his prostate. 

“Touch yourself, Cas. Wanna see you cum, gorgeous,” Dean told him, reaching down to wrap his hand around his own erection. 

His cock was throbbing, the look of pure bliss on his boyfriend's face as he brought himself pleasure bringing Dean closer and closer to the edge. 

“Dean, baby, I miss you so much,” Castiel groaned as pumped his hand around his cock, continuing to fuck himself with his vibrator. 

“I miss you too, Cas. Oh God, baby, you look so fucking good,” Dean breathed out, his palm slick with pre-cum as he jerked himself off. 

“Dean! Oh, yes!” Castiel shouted, arching his hips as an orgasm washed over him, covering his hand and stomach in warm, long ropes of cum. 

“Fuck, Cas!” Dean moaned, getting off at the site of his boyfriend blowing his wad. 

“...So, you still anti-technology?” Castiel panted, gently removing the toy from inside himself. 

“Shut up, Cas. When you suggested that we Skype instead of talk on the phone while you were off on a business trip you didn’t mention anything about sex. If you would have led with that, I would have nearly broken my neck trying to make an account,” Dean teased, leaning back against the headboard of his bed. 

“Nice, asshole. Good to know you didn’t want to Skype with me just to see my handsome face,” Castiel grumbled. 

“That’s not what I meant, baby. You know I love getting to see. I hate it when you’re away…I can’t sleep when you aren’t beside me,” Dean said, reaching up to place his hand on the screen of his laptop. 

“I know, Dean. Don’t worry, babe, I’ll be home soon,” Castiel reassured him, stretching out his hand to Dean as well. 

“I love you, Cas,” Dean cooed, flashing the camera a bright, toothy smile. 

“I love you too,” Castiel replied happily.


	9. Chapter 9

**Notes for the Chapter:**

> Prompt: 9. Against the wall

“…Dean, we can’t…” Castiel protested halfheartedly, letting his boyfriend press his back up against the ally wall that was located behind the night club they had just exited. 

“C’mon baby, please? I need you so bad,” Dean begged, reaching down to palm at Castiel’s erection. 

“Way to fight dirty, Winchester,” Castiel moaned, unable to stop himself from grinding against Dean’s hand,

Smirking, Dean unbuttoned his boyfriend’s pants, quickly tugging them, along with his boxers, down to his ankles, revealing his painfully hard cock. 

“Sorry Cas,” Dean replied, not sounding the least bit sincere as he wrapped his hand around Castiel’s erection and started to stroke him slowly. 

“ _Dean_ …Oh fuck,” Castiel mewled, desperately clawing at the front of his boyfriend’s shirt. 

“Loved watching you in there tonight, grinding against me while we danced,” Dean whispered before kissing Castiel, slow and sensually. 

“Mm, baby, faster,” Castiel begged, thrusting himself into Dean’s hand. 

“Open up,” Dean ordered suddenly, barely giving the other man enough time to do as he was told before he shoved three fingers into his mouth. “Good boy, now suck,” he added, moaning loudly when Castiel began to lick and suck at his fingers, getting them nice and wet with his saliva. 

After a minute or so, once Dean was satisfied that his fingers were slick enough, he then slipped them out of Castiel’s mouth, continuing to jerk him off as he reached down with his spit covered index finger to gently push it into his boyfriend’s puckered hole. 

“Oh fuck!” Castiel groaned, his fingernails digging into Dean’s chest as he began to stretch him open. 

“Desperate baby?” Dean asked cockily, the sound of Castiel’s moans filling his ears when he carefully added a second finger. 

“Yes, Dean please! I need you,” Castiel pleaded, reaching down to undo Dean’s pants, trying frantically to pull them off. 

“Hey, easy Cas. I’ll take care of you,” Dean said, making Castiel whimper when he removed his hand from his cock to tug his pants down the rest of the way. 

“Babe, I’m ready, please,” Castiel told him, threading his fingers through his boyfriend’s hair as Dean slipped a third finger inside him. 

“Yeah, Cas? You ready for my cock?” Dean asked seductively as he circled his fingers around, making Castiel moan when hit his prostate. 

“Yes, please!” Castiel replied, pushing down onto Dean’s fingers. 

“Alright baby,” Dean agreed, slowly pulling out of Castiel before spitting on his palm, getting it as slick as possible so he could stroke himself. 

“C’mon, Dean. I can take it,” Castiel urged, lifting up his right leg to wrap it around Dean’s waist. 

“I know you can, Cas. So good for me,” Dean praised as he lined himself up with Castiel’s hole before pushing in slowly. 

“Fuck,” Castiel whispered under his breath, wrapping his arms around his boyfriend’s neck. 

“You good baby?” Dean questioned once he had bottomed out. 

“Yeah, I’m good. Just move, please,” Castiel replied, shouting his lover's name when Dean began to thrust his hips steadily, making sure to hit Castiel’s prostate with every movement. 

Leaning forward, Dean pulled Castiel into a heated kiss, his boyfriend’s mouth tasting like raspberry from the flavored vodka he had been sipping on earlier that night. 

“I love you, Cas,” Dean mumbled, nipping and sucking at Castiel’s swollen, pink lips. 

“I love you too, Dean,” Castiel replied with his eyes closed tight and a look of pure bliss on his face. “Happy birthday,” he added coyly, starting to move his hips with Dean’s, creating extra friction. 

“Thanks baby…You know, I was thinking...watching you cum with my cock inside you is going to be the best birthday present I could ever ask for,” Dean mused, smirking when Castiel let out a needy whimper as he started to stroke him again. 

“Oh God, Dean!” Castiel moaned, his boyfriend only having to pump his wrist a couple of times before an orgasm ripped through him. 

“ _Fuck_ …That’s it baby, so fucking good for me,” Dean praised, stilling his hips for a moment as he peppered kisses all over Castiel face, his boyfriend leaning back against the wall for support, trying to catch his breath. 

“C’mon birthday boy,” Castiel said seductively, bracing his hands against Dean’s chest. “Your turn.” 

Letting out a soft chuckle, Dean began to move again, biting his bottom lip when he felt a warm sensation pooling in the pit of his stomach. 

“Holy fuck!” Dean growled, thrusting his hips sporadically until he found his release. 

“Feel good baby?” Castiel whispered, running his hands through Dean’s hair when his boyfriend bent forward, nuzzling his face into his neck.

“Hell yeah, you’re so perfect Cas,” Dean mumbled against his skin, taking a few seconds before gingerly pulling out of Castiel. 

“There’s no need for flattery, handsome. I’ve already let you in my pants,” Castiel teased, giving Dean a mischievous smirk when he raised his head up to look him in the eyes. 

“I’m serious, baby. You’re amazing,” Dean said affectionately. 

“You aren’t too bad yourself, Winchester,” Castiel replied before throwing his arms around Dean to give him a warm, comforting hug.

**Notes for the Chapter:**

> It's so fluffy!


	10. Chapter 10

**Notes for the Chapter:**

> Prompt: 10. Doggy Style

After a long, hot, relaxing shower, Castiel got dressed in his pajamas and made his way to the kitchen where his boyfriend Dean was preparing to cook him dinner. 

“Hey baby, feel better?” Dean asked when he saw Castiel enter the room. 

Dean was standing at the island in the middle of the kitchen, wearing nothing but a pair of grey sweat pants that hung low on his hips as he sat a cutting board down on the counter. 

“Much,” Castiel replied happily, walking over to stand behind his boyfriend, wrapping his arms around his waist. “What cha making?”

“Chicken fried steak, mashed potatoes, and yellow squash,” Dean stated, turning his head slightly to the left so he could give Castiel a quick kiss on the cheek. 

“Damn babe…It’s almost 10 p.m., you don’t have to cook me a five course meal. I would be completely satisfied if you just heated up the chicken nuggets we have in the freezer,” Castiel teased, nuzzling close to his boyfriend. 

“Cas, you just worked a double. You deserve a nice, home cooked meal,” Dean told him. 

“Thank you, Dean. That means a lot to me,” Castiel cooed, peppering kisses all over the left side of Dean’s freckled face. 

“…But?” Dean asked, sensing that Castiel was restless. 

“…But, to be honest, food is the last thing I’m thinking about right now,” Castiel explained as he began to rub Dean’s stomach right above the waistline of his pants. 

“Oh?” Dean inquired, leaning back to grind his ass against Castiel’s crotch, noticing that his boyfriend was already half hard. “What exactly are you thinking about then?”

“Truthfully? I was thinking about bending you over this counter and fucking you senseless,” Castiel whispered in Dean’s ear, sliding his hand down to massage his boyfriend’s cock through his sweats. 

“ _Fuck_ , Cas please,” Dean mewled, letting out a sharp little gasp when Castiel turned his head so he could pull him into a rough kiss. 

“Would you like that, Dean?” Castiel asked, biting and sucking at Dean’s full, pink lips. 

“Yes, please baby,” Dean breathed out, rocking back against Castiel’s erection, causing his boyfriend to moan into his mouth. 

“Lean forward,” Castiel ordered softly, releasing his hold on Dean so he could rest his stomach against the counter. 

Once Dean had complied, Castiel began to trail gentle kisses down his boyfriend’s back before sinking to his knees behind him. 

“H-holy shit,” Dean gasped as Castiel pulled down his sweat pants, feeling cool air hit his hot, swollen cock. 

“Fuck, Dean. You look so good like this,” Castiel purred, reaching up to massage Dean’s ass cheeks lightly before spreading them apart, exposing his puckered hole. 

“ _Cas_!” Dean shouted when he felt Castiel flick his tongue over his entrance, lapping at the tight ring of muscle. 

“You like that, babe?” Castiel asked seductively, dipping his tongue into Dean’s hole, making him squirm. 

“Yeah baby, please don’t stop,” Dean pleaded, letting out a needy moan when Castiel smacked his ass playfully. 

“I’ve been thinking about this all day, you know? Couldn’t wait to get home so I could make you feel good,” Castiel told Dean between short, teasing brushes of his tongue over his entrance. 

“Oh God, Cas…I need…” Dean mewled, his cock leaking pre-cum, making a mess all down the side of the cabinet. 

“What do you need, Dean? I’ll give you whatever you want,” Castiel promised, his breath hot against the sensitive flesh of Dean’s ass. 

“I want you inside me, please,” Dean whimpered, pressing back against his boyfriend’s tongue. 

“Fuck babe, I want that too, so much…But I don’t want to hurt you. Just let me go grab the lube really quick,” Castiel said as he got to his feet. 

“Cas, wait,” Dean nearly shouted, lifting himself up so that he could open the top draw of the cabinet, producing a small, clear bottle of lube. 

“Dean Winchester, you dirty fucking slut,” Castiel laughed, taking the lube out of Dean’s hand so his boyfriend could bend over once more. 

“That I am, baby. And you best believe there is also a bottle in the cabinet in the living room, on the shelf in the laundry room, in both of our bathrooms…Oh, and in the guest bedroom,” Dean stated nonchalantly, shooting him a mischievous grin over his shoulder. 

“You’re insatiable,” Castiel teased, shaking his head as he popped open the cap on the lube. 

“Says the man who declined a delicious, home cooked meal after working a sixteen hour shift in favor of bending me over,” Dean shot back, trying desperately not to let out a needy whimper when Castiel slipped his lube soaked index finger inside him. 

“Touché, handsome,” Castiel chuckled as he circled his finger around Dean’s hole, stretching him open. 

“It’s okay sweetheart, we can be nyphos together,” Dean joked, moaning loudly when Castiel added a second finger. 

“Enabling each other’s sex addictions…Sounds like a wonderfully healthy relationship,” Castiel taunted, pumping his fingers in and out of Dean, making sure to hit his prostate with each movement. 

“Oh fuck, Cas…Right there,” Dean moaned, ignoring his boyfriend’s comment as he closed his eyes, feeling Castiel massaging the little bundle of nerves inside him. 

“That feel good, babe?” Castiel asked huskily, adding a third finger. 

“ _Yes_ , but I need more…I need your cock, baby,” Dean groaned, pressing his forehead against the surface of the counter as Castiel continued to work him open. 

“You think you’re ready, handsome?” Castiel questioned, brushing his fingers over Dean’s prostate, causing him to shout out in pleasure. 

“Yes! Please, Cas! Please fuck me,” Dean begged, whimpering when Castiel gently removed his fingers. 

“Alright, babe, alright. I’ll give you what you want,” Castiel told him as he pulled down his pajama bottoms before stepping out of the material. 

Then, he picked up the bottle of lube again to pour a generous amount of the clear liquid into his right palm. 

Once he was done, Castiel tossed the bottle to the side before stroking himself with his slick hand, covering his cock with lube. 

“C’mon, baby! I need you so bad,” Dean urged, letting out a sigh of relief when he felt Castiel line himself up with his hole, pressing the head of his cock past the tight ring of muscle. 

“Is this what you want, babe?” Castiel purred, grabbing both of Dean’s hips as he bottomed out. 

“ _Fuck, yes_!” Dean moaned as Castiel started to roll his hips slowly, taking his time. 

“You feel so good around my cock, Dean…Love being inside you,” Castiel whispered, leaning forward to place soft kisses along his boyfriend’s right shoulder. 

“Oh God, faster baby please,” Dean pleaded, grinding back against Castiel when he picked up the pace of his thrusts. 

“That better, babe?” Castiel asked teasingly, sliding his right hand down from Dean’s hip to wrap it around his throbbing cock. 

“Significantly,” Dean retorted, biting his bottom lip when Castiel began to stroke him lazily. 

“Sassy bastard,” Castiel joked, smirking when Dean started making needy, wanton noises with each thrust of his hips. 

“ _Cas_ …I’m so close,” Dean whispered, his body tingling with pleasure. 

“Then let go, handsome. Cum for me,” Castiel told him, pressing a kiss to his boyfriend’s neck as he felt Dean’s back muscles tense underneath him. 

“Holy fuck!” Dean shouted, thrusting himself into Castiel’s hand until he was boneless and panting. 

“So good for me,” Castiel mumbled against his neck, continuing to roll his hips. 

“Love you baby,” Dean panted, sounding completely wrecked as he smiled over his shoulder at his boyfriend. 

“I love you too, Dean…so much,” Castiel moaned as he found his release as well. 

“Damn, Cas. That was incredible,” Dean said, feeling his boyfriend lean forward to lie against his back, both their chests heaving. 

“It really was…I bet you're glad we skipped dinner, now, aren’t you?” Castiel inquired playfully, kissing Dean’s left cheek. 

“Shut up,” Dean replied lamely, letting out a little whine when Castiel gingerly pulled out of him. 

“…I’m not going to lie, though…I kind of worked up an appetite,” Castiel admitted as he slowly stood up straight. 

“Me too, baby,” Dean confessed, pushing himself up from the counter to turn around so that he was face to face with his boyfriend. “What do you say we clean up and make some chicken nuggets?” he added, flashing Castiel a bright smile. 

“Sounds perfect, babe,” Castiel agreed before leaning forward to press his lips against Dean’s.


	11. Chapter 11

**Notes for the Chapter:**

> Prompt: 11. Dom/sub
> 
> (P.S. Sorry this took me so long to post! I didn't do anything but eat yesterday. ;P And then when I did sit down to write this I spouted out a freaking novel. Lol Anyway, hope y'all enjoy it! And just to let everybody know, this is a continuation of the storyline from prompt 4. :D)

When Dean walked through the front door of his apartment, he had just enough time to drop the large dark green duffle bag that was slung over his shoulder on the ground before his boyfriend Castiel threw himself into his arms, jumping up to wrap his legs around his waist.

“Hey baby,” Dean chuckled, hugging his boyfriend tightly.

“I’ve missed you so much,” Castiel mumbled against Dean’s skin, nuzzling his face into the crook of his neck.

“I missed you too, Cas,” Dean whispered, breathing in Castiel’s scent, the familiar smell of cologne and body wash bringing him a sense of comfort that he had been missing for the last eight months.

Remaining in his boyfriend’s arms, Castiel pulled back to look at Dean’s face, smiling down at him affectionately.

“I see you wore your uniform for me,” Castiel said slyly, bringing attention to the fact that Dean was wearing his camo instead of civilian attire.

“Yeah, I thought about changing but then I remembered how much my army gear turns you on,” Dean teased, sliding his hands down Castiel’s back to give his ass a playful squeeze.

Giving Dean a mischievous smirk, Castiel replied by leaning down to kiss him furiously, threading his fingers through his boyfriend’s short brown hair.

Tilting his head back slightly, Dean returned the kiss, massaging his tongue against Castiel’s as they held onto each other for dear life.

“Dean,” Castiel moaned, finally breaking the kiss a few minutes later when he was forced to come up for air.

“Jesus, baby. You have no idea how much I’ve missed this…How much I’ve missed you,” Dean told him, pulling Castiel into another warm, affectionate hug.

“I love you, Dean. I’m so glad you’re home,” Castiel whispered as the massaged the base of Dean’s skull with his fingertips.

“I love you too, sweetheart,” Dean cooed, peppering soft, sweet kisses down his neck.

“C’mon, babe. Let’s go upstairs so you can get a shower and relax,” Castiel suggested, reluctantly untangling his legs from around Dean’s waist to stand in front of him.

“Damn, first my drop dead gorgeous boyfriend greets me at the door with one hell of a welcome home kiss and now I get to take a shower with water that actually gets hot, plus afterward I get to lie down on a mattress that isn’t paper thing? And people say paradise doesn’t exist,” Dean joked as he took Castiel’s outstretched hand, lacing their fingers together. 

“You’re easily amused, Winchester,” Castiel teased, leading Dean to the bathroom with a huge smile on his face.

 

 

**_OoOo_ **

 

 

“ _Cas_ ,” Dean said breathlessly, entering their bedroom to find that his was boyfriend completely naked, kneeling on the floor in front of the bed.

“Sir,” Castiel replied in a sensual tone, careful not to lift his gaze up from the carpet.

Taking in the sight before him, Dean noticed that Castiel was trembling with anticipation, his cock already hard and leaking pre-cum.

“Good boy,” Dean praised before licking his lips hungrily.

Then, without further hesitation, he dropped the towel that was around his waist, beads of water rolling down his chest and back from his recent shower as he walked over to stand in front of Castiel. Out of the corner of his eye, Dean noticed that there was a large, half empty bottle of lube sitting on the bedside table near his side of the bed and that his boyfriend had laid out two of his favorite neckties on his pillow.

“Are you eager to play, baby? You have permission to answer me,” Dean told him, reaching forward to run his fingers through Castiel’s messy black hair.

“Yes Sir, _please_. I need you,” Castiel whispered, leaning into his boyfriend’s touch.

“How long have you been planning this, Cas?” Dean asked, gently sliding his fingertips down the side of Castiel’s face before cupping his chin in his hand, tilting it back so he could look him in the eyes.

“ _Months_ ,” Castiel purred, his pupils blown out with lust as he stared up at Dean longingly.

Closing his eyes, Dean bit his bottom lip to hold back a moan that threaten to escape his throat, the heat of Castiel’s words sending a shiver up his spine.

“Well, now that I’m here, what’s next?” Dean questioned playfully when he regained his composure, brushing his thumb across Castiel’s flushed cheek.

“Anything you want, Sir,” Castiel replied submissively as he ducked his head again, the action going straight to Dean’s cock.

“Stand up,” Dean ordered, smirking when his boyfriend complied instantly.

Once on his feet, Castiel let his hands hang at his sides, keeping his eyes on the floor as he waited for Dean’s next command. 

“So good for me, baby,” Dean cooed, reaching out to wrap his hand around Castiel’s erection, stroking him lazily.

“Fuck, _Dean_ ,” Castiel moaned as he began to rock his hips forward, instinctively resting his palms flat against Dean’s chest.

It had been a full eight months since Dean had touched Castiel like he was at that moment and just the simple feel of his boyfriend’s hand around his cock was driving him crazy.

“Did I give you permission to touch me, Cas?” Dean questioned suddenly, stopping mid-stroke to look at Castiel, his green eyes smoldering.

“N-no,” Castiel said quietly, dropping his hands and his gaze downward.

“No what?” Dean asked his voice low but powerful.

“No Sir,” Castiel corrected, his skin breaking out with goosebumps when Dean resumed his previous action.

“That’s better, Cas,” Dean told him, leaning forward to place a chased kiss to his lips. “But if you misbehave again I’ll have to punish you.”

“Yes Sir,” Castiel whimpered, digging his fingernails into his palms to stop himself from reaching out to touch Dean as his boyfriend continued to jerk him off.

“Perfect. Now, tell me baby. Did you lay those ties out because you want to be restrained? You want those pretty little wrists of yours tied to the bed while I fuck you hard enough to make you scream?” Dean growled, running his thumb over the head of Castiel’s cock.

“Yes, Dean please!” Castiel begged, absentmindedly reaching out to touch his boyfriend once more.

“Castiel,” Dean chided, grabbing him by both wrists.

“It was an accident Sir,” Castiel said, his cock throbbing because of the dominant tone of Dean’s voice.

“Look at me,” Dean demanded.

Complying, Castiel looked into Dean’s eyes, chocking back a needy moan at the sight of the handsome, powerful man in front of him.

“Are you going to punish me, Sir?” Castiel asked timidly, trying his best to hold Dean’s gaze.

“Yes baby. Now, get on your hands and knees on the bed with that sexy ass of yours facing toward me,” Dean ordered before releasing Castiel’s wrists.

Once free, Castiel turned around to crawl onto the foot of the bed so that he was positioned as Dean had instructed.

“Like this, Sir?” Castiel questioned innocently, whimpering when he felt Dean’s fingers digging into his skin, groping his ass cheeks.

“…How long have you been wearing this?” Dean inquired breathlessly, ignoring Castiel question upon noticing the latex plug that was inserted in his boyfriend’s ass.

“I put it in right before you got home, Sir…” Castiel explained, moaning like a porn star when Dean removed the plug, which was slick with lube, in order to pump it in and out of his hot, wet hole.

“Holy fuck, just you wait baby. After I’m done punishing you I’m going to tie you to this bed and fuck you until you can’t remember your own name,” Dean said, his words sounding like something between a threat and a promise.

“Sir, _please_ ,” Castiel mewled, a wave of disappointment washing over him when Dean stopped moving the plug.

“Shh, Cas. Now, tell me why you are being punished,” Dean demanded, trailing his fingertips lightly over Castiel’s lower back.

“…Because I touched you without permission,” Castiel answered, his body aching with need as pre-cum dripped down his thighs.

“And?” Dean asked, moving his hand to rest it on Castiel’s right ass cheek.

“…And because I didn’t address you as ‘Sir’,” Castiel added, gripping the sheets beneath him tightly with both hands.

“Very good. And since we haven’t played in a while and you are out of practice, I’m only going to spank you ten times. Does that seem fair, Cas?” Dean inquired.

“Yes Sir,” Castiel replied urgently.

“I want you to count them for me, baby,” Dean told him before drawing back his hand to smack Castiel on the ass forcefully.

“One,” Castiel moaned, his skin already starting to tingle as Dean raised his hand to deliver a second smack.

Between each blow, Dean massaged the heated, overstimulated flesh of Castiel’s ass check, reducing him to a babbling mess by the time he was done.

“T-ten,” Castiel gritted out, trying desperately not to cum on the spot when Dean administer his final spanking.

“Good boy. You were so perfect for me, Cas,” Dean praised, bending down to run his tongue over one of the hand prints visible on Castiel’s ass.

“Please Sir, I need you! Fuck me, please,” Castiel pleaded, not sure how much longer he could last.

“I will, baby, just hold on,” Dean purred as he removed the plug from Castiel’s ass. “Now, lay on your back for me. And lift your arms above your head,” Dean ordered, letting out a soft chuckle when Castiel immediately crawled forward to do as he was told.

Laying on his back in the middle of the bed, Castiel took a few seconds to get comfortable before he raised his arms up over his head, watching intently as Dean grabbed one of the ties that was on his pillow to wrap it around his right wrist so that he could secure it to the headboard.

“Whoa there Army man,” Castiel blurted out suddenly when Dean began to tie an inescapable knot.

“Civilians,” Dean teased, tugging at his handy work to make sure it was secure before moving onto Castiel’s other wrist.

“Well if anything, I am now overly aware that your years of dedication and service to this country have made you one badass knot tier,” Castiel shot back, attempting to move his wrists when Dean done but having absolutely no luck.

“Easy Cas. I let your first comment go but you're pushing it,” Dean warned as he reached over to grab the bottle of lube that was on the bedside table.

“Sorry Sir,” Castiel apologized, not wanting to give his boyfriend another excuse to keep teasing him.

“Damn, you must be desperate for me to fuck you if I’ve silenced that sarcastic mouth of yours,” Dean taunted, popping open the cap on the lube to pour a generous amount of the clear liquid into his right hand.

“You have no idea how bad I want you to fuck me… _Sir_ ,” Castiel retorted, gasping when Dean slipped two fingers inside him.

“Oh, I think I have a pretty good understanding, baby boy,” Dean chuckled as he found his boyfriend’s prostate, massaging the tiny bundle of nerves with his fingertips.

“Dean please! I’m ready,” Castiel whined, arching his hips off the mattress.

“I know Cas, but I want to take my time. You aren’t the only one whose been fantasizing about this moment for the last eight months,” Dean confessed, adding a third finger.

“Oh fuck,” Castiel groaned, pre-cum oozing down the shaft of his cock as Dean worked him open.

“God, I’ve missed this….I’ve missed everything about you,” Dean whispered a few moments later, finally removing his fingers from Castiel, causing his boyfriend to let out a small whimper.

“Me too, Dean. I’m so happy you’re home,” Castiel told him, grateful when Dean bent down to give him a soft kiss on the lips.

“…You know…When I was on tour, sleeping in some God-forsaken desert, not knowing whether or not I’d live to see the next morning…The thought of your touch…getting to see your beautiful face again, to hold you in my arms…That was the only thing keeping me going,” Dean admitted suddenly, causing Castiel to stare at him in awe.

“…Dean, you’re home now babe. We’re together and you’re safe,” Castiel said soothingly, sitting up as far as his restraints would let him so he could kiss Dean once more.

“I know, baby…I know,” Dean whispered, resting his forehead against Castiel’s.

“I love you, Dean,” Castiel declared, rubbing the tip of their noses together playfully.

“I love you too, Cas. More than you’ll ever know,” Dean replied, giving him one last peck on the lips before rocking up onto his knees so that he could wrap Castiel’s legs around his waist.

“C’mon, babe. Fuck me so damn good that it will make up for all the time we've been apart,” Castiel purred, shooting Dean a sly grin.

Smiling back, Dean reaching down to wrap his hand around his erection, lining himself up with Castiel’s entrance before pushing in agonizingly slow.

“Holy fuck, baby. I almost forgot how amazing it feels being inside you,” Dean moaned as he bottomed out.

“Oh God, Dean… _Yes_ ,” Castiel nearly yelled when Dean began to roll his hips, his thrusts deep and hard, but at the same time slow and methodical.

“You look so fucking beautiful right now Cas…I love it when you let me take control like this, love that you’re so desperate for it,” Dean told him, reaching down to stroke his boyfriend’s cock.

“Dean,” Castiel mewled, watching as Dean continued to fuck him, his stomach muscles flexing with every thrust of his hips as beads of sweat rolled down his chest.

“You close, baby boy?” Dean asked when Castiel let out an animalistic moan, throwing his head back against his pillow.

“Yes! Fuck, Dean I’m…” Castiel shouted, unable to complete his thought before one of the most intense orgasms he had ever experienced washed over his body.

“Cas!” Dean cried out a few seconds later, thrusting his hips on last time before he found his release as well.

“…Holy fuck, babe,” Castiel panted, his body tingling with pleasure as his boyfriend laid his head on his chest.

“I know, baby. God, I needed that,” Dean replied, pacing a tender kiss to Castiel’s left pectoral above his rapidly beating heart.

“Me too…That was amazing,” Castiel sighed happily as Dean sat up to untie his wrists.

“Hell yeah it was,” Dean chuckled, shooting his boyfriend a playfully wink when he was done with his task. “You okay?” he added, examining Castiel’s slightly bruised skin.

“Now that you’re home, I’m fantastic,” Castiel said, surging forward to wrap his arms around Dean’s neck.

“I’m glad to hear that baby, and I’m so damn happy to be home,” Dean told him, nuzzling against Castiel’s shoulder as he hugged him back.


	12. Chapter 12

**Notes for the Chapter:**

> Prompt: 12. Fingering
> 
> I'm sorry this is so short! :( And I'm sorry about the lateness of my updates. My final semester of college might be the end of me. Lol 
> 
> Anyway, I hope y'all enjoy!

“ _Jesus_ …For fuck’s sake, Winchester, quit messing around,” Castiel huffed, digging his fingernails into the tops of Dean’s bare shoulders. 

“Stop bitching, Cas. You fucking love it,” Dean taunted as he pumped three fingers in and out of Castiel, deliberately dragging them over his prostate with every movement. 

“ _Dean_ , please,” Castiel begged, the other man's action setting his blood on fire. 

By that point, Castiel was so painfully hard that he felt as though he might die before Dean finally decided to fuck him. 

“You’re so desperate for me to fuck you, aren’t ya Cas?” Dean questioned teasingly. 

Rolling his eyes, Castiel was hardly able to hold back a groan at the smugness in Dean’s voice. 

“I hate you,” Castiel gritted out, his cock throbbing as Dean crooked his fingers to the side, massaging the tiny bundle of nerves inside him. 

“Bullshit, baby,” Dean shot back, reaching up with his free hand to wrap it around Castiel’s erection. 

“Oh fuck, Dean,” Castiel mewled, his grip on Dean’s shoulders tight enough to bruise. “Babe, if you don’t stop I won’t be able to last much longer,” he added before a loud, guttural moan escaped his throat in response to Dean leaning forward to lick the tip of his cock. 

“That’s okay baby, I want you to let go. Don’t worry about me; I just want to make you feel good,” Dean purred as he continued to finger Castiel, jerking him off slowly in the process. 

“Dean, oh God...” Castiel said breathlessly, a warm sensation pooling in pit of his stomach. 

“C’mon Cas, wanna see you cum around my fingers. Wanna hear you scream my name,” Dean coaxed, watching intently as Castiel arched his hips up off the mattress. 

“Holy fuck, Dean!” Castiel yelled, his eyes rolling back in his head as an orgasm ripped through his body. 

“That’s it, baby,” Dean praised, continuing to stroke Castiel’s cock while long, hot ropes of cum dripped down his knuckles. 

“…Damn babe,” Castiel whispered when Dean had finally worked him though his orgasm. 

Relaxing his body against the bed, Castiel let out a calming breath, his skin tingling with a warm, deliciously indescribable sensation. 

He absolutely loved times like this. 

He loved that, ever since the very beginning of their relationship, Dean’s sole focus in the bedroom had been making sure Castiel was taken care of. Dean wasn’t about mindless fucking or his own pleasure, he was all about making his partner feel good and Castiel fucking love it. 

It was no secret that he had been with a few people before Dean, but Castiel stood by his claim that none of his previous lovers could compare to the way Dean made him feel during sex. 

It was downright euphoric. 

“Fuck, I love watching you cum, Cas,” Dean said, sounding completely wrecked. 

“Of course you’d love admiring your own handy work,” Castiel teased, wincing a little when Dean removed his fingers from inside him. 

“…Shit baby…You caught me, I don’t even have a comeback for that,” Dean chuckled as he rocked himself upward so that his face was inches away from Castiel’s. 

“Whoa, Dean Winchester at a loss for words? Someone call the press,” Castiel joked, letting out a small laugh before Dean silenced him by pressing their lips together.

“Smartass,” Dean mumbled into the kiss. 

“True, but you like it,” Castiel purred, nipping at his bottom lip as he slid his hand between their bodies, wrapping it around Dean’s erection which was dripping with pre-cum. 

“…That’s two for two…You’re on a roll, baby,” Dean jeered, but when Castiel began to stroke his cock, his sarcasm turned into loud, needy moans.


	13. Chapter 13

**Notes for the Chapter:**

> Prompt: 13. Rimming
> 
> ...So...This is basically a product of the residual effects of prompt 11...And I kind of went a little crazy with this...Lol 
> 
> Sorry these updates are taking so long. I graduate in 13 days and RL has been CRAZY.

“Something you need, Mr. Winchester?” Castiel asked gruffly, not bothering to look up from the deposition he was reading. 

He was aware of Dean’s presence because he had heard him shuffle into his office, but the younger man had failed to address him for several minutes and it was starting to make Castiel feel a little uncomfortable that he was just standing there, staring at him. 

“N-no sir!…I mean, y-yes sir…I-,” Dean stuttered, causing Castiel to lift his gaze ever so slightly. 

“Which is it Mr. Winchester? Yes or no?” Castiel inquired, trying to ignore the fact that his cock twitched at the sight of Dean lowering his head submissively in response. 

“…It’s not that I _need_ anything, sir…I just wanted to know if you’d like me to go pick you up something for lunch. It’s almost one thirty and I know when you get busy you forget to eat…” Dean babbled, his cheeks a bright shade of red. 

Letting out a small sigh, Castiel set back in his reclining office chair, studying Dean curiously with his vibrant blue eyes. 

Dean had started working for Castiel not even three months prior and already he knew his habits. He was dutiful, attentive, and even though he was barely twenty three, the young man had impeccable work ethic. Honestly, Dean was the only secretary Castiel had ever enjoyed having around. Perhaps his admiration for the young man had a little bit to do with the fact that Dean was kind and patient with him, even when Castiel was being a gigantic asshole. Who knew? 

However, what Castiel did know for certain was just how much he loved his secretary's obedient, submissive nature. Dean did things Castiel’s way, no questions, no complaints. And, if Castiel was being completely honest with himself, he damn near got off on it. 

While it was no lie that his four previous secretaries, who had all been fired within a week of working for Castiel, would probably say that he was an evil dictator with a superiority complex, Dean was different. He didn’t seem to mind Castiel’s over-baring, micromanaging tendencies, no matter how hard the older man pushed him. 

“That’s very thoughtful of you, Mr.-…Dean...I’d love something to eat,” Castiel said eventually, causing Dean to look up at him, a smirk tugging at the corner of his full, pink lips. 

“…What are you hungry for, sir?” Dean replied immediately in a low, almost feral, tone and it was all Castiel could do to hold back a moan that threated to escape his throat. 

It was not usual for Dean to make suggestive comments like that, the younger man had never hidden his attraction to Castiel, not even when he had interviewed him for his position. However, barging into Castiel’s office and trying to seduce him was a bit brazen, even for his young secretary.

“Are you deliberately trying to bait me, boy?” Castiel asked sternly, his cock already half hard at the sight of Dean lowering his gaze to the floor again, the younger man’s chest heaving as he fiddled with one of the buttons on his blue, long sleeve dress shirt. 

Truthfully, Castiel enjoyed Dean’s flirtations. It was an enormous boost to his ego that such a gorgeous young man, who was in the middle of a master’s program and had everything going for him, would want a forty-two year old, very stubborn and equally as controlling, lawyer such as himself. Nevertheless, he was not about to let Dean know how much he wanted him as well. Castiel was going to play it cool, make Dean sweat. It was just in his nature. He needed to have the upper hand in all situations. 

“…Y-yes sir,” Dean admitted, his voice all but a whisper as he shifted awkwardly from one foot to the other.

The secretary could practically feel the embarrassment wash over him when he realized that his erection was visible through his slacks. 

“What was that, Mr. Winchester? Speak up,” Castiel demanded, pushing his chair back from his desk so that there was a small space between his knees and the wooden structure. 

“I said _yes sir_ ,” Dean repeated nervously, daring to sneak a peek at the older man. 

“Shut and lock the door, Mr. Winchester,” Castiel ordered as they locked eyes. 

Dean’s breath hitched in his throat when he saw that Castiel’s pupils were dilated, only a hint of blue visible, as he stared at him with pure, unadulterated lust. 

“You’ve never disobeyed me before, Mr. Winchester…Are you going to start now?” Castiel asked roughly, snapping Dean out of his trance. 

It was then that Dean realized he was still standing in front of Castiel, his mouth slightly open, panting as though he had just run an Olympic race. 

“No! Of course not,” Dean stammered, turning around quickly to shut Castiel’s office door before flipping the lock. 

Once the door was secure, Dean looked over at Castiel eagerly, his legs trembling in anticipation. 

“Good boy,” Castiel praised, his voice smooth as honey, sending a shiver of pleasure up Dean’s spine. 

“What do you want me to do now, sir?” Dean asked innocently. 

“Take off your clothes, Mr. Winchester. Slowly,” Castiel told him as he slid his right palm over the bulge in his pants, massaging his erection lightly. 

With trembling hands Dean obeyed, taking his time as he undid the buttons on his shirt. Biting his bottom lip, he then pulled the material off his body, shooting Castiel a smoldering look as he dropped the shirt on the floor. 

“Is this what you want, sir?” Dean inquired, sliding his hands down his stomach teasingly before popping open he button on his slacks. 

“Exactly. Keep going Mr. Winchester,” Castiel replied breathlessly, continuing to palm at his erection. 

Giving Castiel a quick nod, Dean slipped out of his shoes before unzipping his pants to pull them down, revealing the pair of red boxers he was wearing. He was painfully hard by that point and the brightly colored fabric was soaked with pre-cum where his erection was pressing against the front of his underwear. 

“I know I told you to go slow, Mr. Winchester…but I don’t have all day,” Castiel said impatiently when Dean hesitated to take the next step. 

“Sorry sir,” Dean apologized, anxiety getting the better of him as he shook from head to toe. 

It wasn’t that he had qualms about continuing, because holy fuck did he want to. It was just that Dean couldn’t believe this was happening. He had been fantasizing about his boss for months now and all of a sudden his fantasies were coming true. And to categorize the situation he was currently in as overwhelming would have been a gross understatement. 

Letting out a deep breath, Dean took a second to gather his wits before stepping out of his pants in order to kick the material to the side. He then quickly removed his socks, tossing them over to join the pile of his cloths on the floor.

“Mr. Winchester, do you enjoy toying with me?” Castiel asked sharply, the hand of his cock stilling for the moment as he looked at Dean intently. 

Contemplating his answer, Dean ran his fingertips along the elastic of his boxers playfully. On one hand, he couldn’t deny that he liked seeing Castiel, who always had his emotions in check, now sitting before him, every part of his body screaming with desire. However, on the other, Dean wasn’t sure if admitting such a thing would be well received by his unyielding boss. 

“…Yes sir…I do,” Dean confessed sheepishly after a short deliberation. 

“Take off your boxers, you filthy little tease. And come over here,” Castiel demanded hotly, his whole body tensing as though he were trying to hold himself back from ravishing Dean on the spot. 

Not needing to be told twice, Dean pulled down his underwear, stepping out of the material as fast as he could before heading over to Castiel. 

“Fuck, you’re gorgeous,” Castiel whispered when Dean was finally standing in front of him. 

The younger man’s whole body was flushed, the redness of his skin making his freckles more pronounced. His hands were at his sides but Castiel could see that he was itching to touch him and he loved how riled up Dean looked despite the fact that they hadn’t even done anything yet. 

“…Thank you, sir…” Dean replied shyly, looking down at Castiel with his florescent green eyes which were hooded with lust.

“Turn around and lay with your stomach flat on my desk,” Castiel commanded, his patience wearing thin. 

“B-but sir,” Dean managed to stuttered before the older man was on his feet, wrapping his right hand around Dean’s throat. 

“I gave you an order, Mr. Winchester. Now be a good little slut and follow it,” Castiel growled, leaning forward to take Dean’s bottom lip between his teeth, tugging roughly at the sensitive skin. 

“Yes sir, right away,” Dean whimpered, shuddering as a bead of pre-cum rolled down his throbbing cock. 

He was almost embarrassed at how hard he was for his boss, unable to believe that he was so turned on by being told what to do. 

Up until that point, Dean had never shown his submissive side during a sexual experience. Not to mention that, even though he knew he was bisexual and didn’t try to hide it, his only other encounter with a man apart from Castiel was a short, drunken make out session at a college party during his first semester. 

“That’s what I like to hear. Don’t worry, baby boy. As long as you obey me, I’ll make this so good for you,” Castiel purred, releasing the younger man so he could turn around. 

Trying not to freak out, Dean laid down on Castiel’s desk, exposing his ass to the man behind him as he spread his legs slightly to support his weight. 

“Please sir,” Dean begged, not exactly sure what he was asking for. 

All he knew was that he was mad with want, his cock trapped between his stomach and the cool mahogany, aching to be touched. 

“Mm, that’s it handsome. Now you're getting the picture,” Castiel teased before delivering a playfully smack to Dean’s right ass cheek. 

“Fuck, Castiel please!” Dean mewled, gasping when Castiel grabbed a handful of his short brown hair, pulling it hard. 

“Did I give you permission to say my name?” the older man asked venomously, leaning forward to pressing his erection between Dean’s ass cheeks. 

“No sir!” Dean gritted out, Castiel’s dominant nature spending a spark of electricity through his veins. 

“You will address me as 'sir' until I tell you otherwise, do you understand me?” Castiel inquired before sinking his teeth into Dean’s right shoulder, causing the younger man to let out a strangled moan. 

“Yes sir, I understand. I understand,” Dean babbled, an odd mixture of pleasure and pain consuming his senses. 

“Good boy. I also want you to keep your voice down, Mr. Winchester. Under any other circumstances I’d be thrilled to hear you scream like the wanton little slut that you are, but not here. I’d be furious if my colleagues overheard you making noises that are only meant for me. Right, baby? Those filthy little moans are all for me, aren’t they?” Castiel asked as he rocked his hips against the younger man’s ass, causing Dean’s cock to slid against his stomach and the desk, creating much needed friction. 

“Yes sir! Only for you,” Dean groaned. 

“I know, baby boy,” Castiel cooed before standing up straight and taking a step back so he was no longer touching Dean. 

“Sir!” Dean protested, feeling as though he might explode if Castiel didn’t stop his teasing. 

“Don’t whine, Mr. Winchester. I don’t like it,” Castiel chastised and Dean immediately fell silent. “Perfect. So good for me. Now, hold yourself open,” the older man demanded. 

“W-what?” Dean asked without thinking, desperately trying to hold back a moan when Castiel slapped his ass again, this time with force.

“Do as you’re told, Mr. Winchester,” Castiel spat and although Dean couldn't see him, he knew he had a dangerous, calculating look on his face. 

It was the same look that Castiel gave his opponents in the courtroom, the same look that could make a full grown man tremble with fear. 

“I’m sorry, sir. I’ll be good for you, I promise,” Dean whispered as he reached back with both hands to spread his ass cheeks apart. 

“I know you will, slut. Because the next time you disobey me, there will be consequences,” Castiel threatened before dropping to his knees behind Dean. 

“H-holy fuck!” Dean shouted when he felt Castiel’s tongue circle around his entrance. 

“Mr. Winchester,” Castiel chided, digging his fingernails into the backs of Dean’s thighs. “I told you to keep your voice down.” 

“I’m sorry, I’m sorry. Please sir, I’ll behave,” Dean pleaded desperately. 

“Shh, baby boy. I believe you. But if you are lying, I promise you will not like your punishment,” Castiel told him before dipping his tongue inside Dean’s puckered hole. 

“Oh God…Sir, that feels _amazing_ ,” Dean panted, relaxing when Castiel’s grip on his legs turned to gentle caresses. 

“I knew you’d like this, baby boy,” Castiel purred as he lapped at Dean’s ass, coating the ring of muscle with his saliva. 

“…Sir, please…” Dean begged, embarrassingly close to coming untouched. 

“My goodness, Mr. Winchester. You’d think with how desperate you sound that you’d never been touched like this before,” Castiel taunted before swirling his tongue around, making Dean curse under his breath. 

“…I haven’t…sir,” Dean admitted, his mind fuzzy with lust. 

“Really?” Castiel asked skeptically. “Forgive me Mr. Winchester but I can’t imagine that any one of your previous sexual partners passed up the opportunity to eat out this sexy little ass of yours,” he added, his voice completely wrecked as he lifted his right hand to tease Dean’s hole with the tip of his index finger. 

“ _Fuck_ …I never…You’re the first…” Dean mumbled incoherently, every one of his nerve endings tingling with desire. 

“…What? Dean, are you trying to tell me you’ve never been with a man before?” Castiel asked as he sat back on his heels, earning a needy whimper from the younger man at the loss of his tongue. 

“…Yes sir…” Dean confessed, silently hoping that his inexperience wouldn’t detour Castiel’s advances. 

“…Jesus Christ…” Castiel muttered under his breath as he got up to sit in his office chair. 

“Sir, please. I want you,” Dean said urgently, pushing himself up off the desk so that he could face the older man. 

“…Dean, enough. You don’t want your first time to be with some guy you barely know...Besides, I'm nineteen years older than you for God's sake. You deserve better,” Castiel sighed, rubbing his eyes wearily. 

“Si-…Castiel…please don’t tell me what I do or do not want. That is for me to tell you. Only I know that,” Dean stated firmly, his green eyes boring into Castiel’s blue ones. 

Staring back, Castiel’s expression soften, his heart swelling with pride at the sight of Dean bravely standing in front of him with his chin held high. 

“…You’re right, Dean. Please forgive me,” Castiel apologized, getting up from his seat to cup both of Dean’s cheeks in his hands. 

“You’re forgiven Castiel…I couldn’t stay upset with you if I tried,” Dean admitted, leaning into the older man’s touch. 

“…You never cease to amazing me, Mr. Winchester…I’m lucky to have you as my employee,” Castiel said before pulling the younger man into a passionate kiss. 

Returning the kiss, Dean wrapped his arms around Castiel’s neck as he pushed his tongue into his mouth. 

“Sir, please…Show me how much you appreciate me, how lucky you are to have me,” Dean moaned, nipping at Castiel’s bottom lip. 

“Get back on the desk,” Castiel growled, gently pushing Dean away from him. “No, on you back this time. I want to see that pretty face of yours,” he added when Dean made a move to turn around. 

Smirking, the younger man complied, sitting on the edge of Castiel’s desk before laying back and spreading his legs. 

“Perfect, you’re perfect baby boy,” Castiel praised before slipping three of his fingers in his mouth to coat them with spit. 

Once he was satisfied that they were wet enough, he moved forward, lifting Dean’s legs up so that his ass was exposed. 

“This might sting a little, baby. I wish I had the strength to wait until we had lube, but I’m going crazy not being inside you,” Castiel admitted, gently pressing his index finger against Dean’s hole. 

“It’s okay, please! I need you,” Dean begged, letting out a sharp gasp when Castiel pushed his finger inside him. 

“Shh, that’s it Dean. Relax, it will feel better soon, I promise,” Castiel purred as he worked Dean open. 

“ _Motherfucker_ ,” Dean moaned, arching his hips when the older man found his prostate. 

“You like that, baby?” Castiel asked, adding a second finger. 

“Y-yes sir,” Dean whispered, a look of pure pleasure on his face. 

There was no denying that what Castiel was doing hurt a little, but whenever the older man hit his sweet spot with his long, smooth fingers, the pain was well worth it. 

“Jesus, Dean…You are breathtaking…Wish you could see how good you look stretched out around my fingers,” Castiel panted, slipping a third finger inside Dean. 

“S-sir,” Dean moaned, urging Castiel on. 

“…You may use my name, baby boy. If you’d like,” Castiel said in a soft tone as he massaged Dean’s prostate gently with the tips of his fingers. 

“…C-Castiel, _please_! I need you,” Dean begged, whimpering when Castiel removed his fingers gingerly. 

“Hold on, Dean. I’ll give you what you want,” Castiel promised as he quickly undid his belt, tossing it to the side before pulling down his pants and boxers to reveal his large, swollen cock, slick with pre-cum. 

“…Fuck Castiel…You’re huge,” Dean panted, his voice dark with lust. 

“Like what you see, baby boy?” Castiel asked, earning an enthusiastic nod from the younger man. “Use your words, Mr. Winchester. Tell me what you want,” he added, chuckling at how flustered Dean was. 

“For fuck’s sake, Castiel! Fuck me, please!” Dean gritted out, clawing at the desk beneath him when Castiel grabbed his legs roughly and lifted them straight up. 

“I’m not sure how much I like this new attitude of yours Mr. Winchester,” Castiel teased before spitting on his palm in order to stroke himself so that his cock was slick with a mixture of pre-cum and saliva. 

“I’m sorry, sir. Please! I’ll do whatever you want…Please, please!” Dean mewled, completely consumed by desire. 

“Fuck…That’s what I like to hear, baby,” Castiel growled as he lined himself up with Dean’s entrance, playfully circling the head of his cock around the tight ring of muscle. 

“Sir, please! I need to feel you inside me, want you so bad,” Dean implored, sounding almost frantic. 

“…Are you sure, Dean? You truly want this? Truly want me?” Castiel questioned, preparing himself for the possibility that the younger man would come to his senses and call the whole thing off. 

“Castiel, look at me,” Dean ordered, trying to gather enough composure to address his boss with conviction. 

Obeying, because something deep down inside him urged him to do it for Dean, Castiel locked eyes with the younger man, his heart pounding rapidly in his chest. 

“I want _you_ , Castiel. I’ve wanted you from the minute I laid eyes on you,” Dean confessed and something about the tone of his voice made Castiel believe that he was telling the truth. 

“Okay, baby. That’s all I needed to hear,” Castiel said smoothly before pushing into Dean at an agonizing slow pace. 

“Oh fuck, oh fuck,” Dean babbled incoherently, that odd mixture of pleasure and pain coming back tenfold as Castiel bottomed out. 

“Mm, you’re quite the poet Mr. Winchester. Who knew?” Castiel chuckled, running his hands up Dean’s chest sensually, stalling in order to give the younger man some time to adjust to the new sensation. 

“I know, right? That was Walt Whitman status, was't it?” Dean shot back as reached up to thread his fingers into Castiel messy black hair. 

“You’re funny, I’ll give you that baby,” Castiel taunted, leaning down to place a chased kiss to Dean’s collar bone. 

“That’s mighty sweet of you, sir,” Dean replied coyly. “…I think I’m ready for you to move now,” he added, clenching around the older man’s cock, causing him to let out a low growl. 

Remaining silent, Castiel pulled out of Dean until only the head of his cock was still inside him before thrusting his hips forward, re-filling the younger man in one swift motion. 

“You like that?” Castiel asked smugly when Dean failed to hold back a filthy, desperate moan. 

“Y-yes!” Dean said breathlessly as Castiel began to pound into him, the older man’s fingers digging into the tops of his thighs, grasping them for leverage. 

“Yes what?” Castiel asked in a demanding tone, thrusting into Dean hard and deep. 

“Yes sir! Oh fuck!” Dean groaned, his grip on Castiel’s hair tightening. 

“Touch yourself, baby boy. I want to watch you fall apart as I fuck this sexy virgin ass of yours,” Castiel told him, reveling in the feeling of his cock sliding in and out of Dean’s hot, tight hole. 

“ _Castiel_ ,” Dean whimpered as he reached down to stroke his cock at a quick pace. 

“Oh God, Dean…Love hearing you say my name,” Castiel admitted, smirking when he saw Dean’s whole body tense as the younger man arched his hips up off the desk. 

“H-holy fuck, Castiel,” Dean nearly shouted as an orgasm washed over him, splashing long, hot ropes of cum all Castiel and himself. 

“Dean!” Castiel called out a few seconds later, the sight of Dean coming undone beneath him enough to send him over the edge. 

Moaning, Dean dug his fingernails into the tops of Castiel’s shoulders, unable to deny that he loved the feeling of the older man’s cum filling him up, the warm, sticky sensation turning his insides to Jell-O.

“…That…Fuck, that was incredible…sir,” Dean panted, letting out a barely audible whimper when Castiel slid out of him carefully. 

“Yes, it was quite enjoyable,” Castiel replied, sounding far more professional than he meant to as he bent down to pull up his pants. 

Sitting up, Dean eyed the older man cautiously, watching him as he plopped down in his office chair.

“…Perhaps next time you should remove all of your clothes, sir…” Dean suggested timidly, causing Castiel to look down at his wardrobe. 

Examining himself, Castiel quickly realized that he was a mess. His shirt was stained with cum, not to mention drenched in sweat and his pants were wrinkled from when they were pooled around his ankles. 

“Next time? That’s awfully presumptuous of you, Mr. Winchester,” Castiel scolded, trying not to react when Dean hoped off his desk to promptly sit in his lap. 

“…But I was good for you, wasn’t I sir?” Dean purred as he wrapped his arms around Castiel’s neck, nuzzling one of his freckled cheeks against the older man’s jaw.

“Mm, I think you know the answer to that, baby. And that’s why you’re acting so cocky,” Castiel replied, causing Dean’s breath hitch in his throat. 

It was true. Dean was highly aware that he had just barely followed Castiel’s orders and despite that fact, the older man had let him get away with it without punishment. He was the only person Castiel showed leniency toward and having him seemly wrapped around his finger only served to inflate Dean’s ego. 

“Maybe so…” Dean mused, trying to seem unfazed. “Which is all the more reason you should fuck me again, teach me how to behave properly. Show me that bad boys like me _actually_ get punished if they disobey.”

“…Very well, Mr. Winchester,” Castiel agreed, his voice slightly strained. “I’d be thrilled to make you submit to me fully…Would you like that, baby? To let me use your body any way I wanted? For me to give you pleasure like you’ve never felt before?” he added in a whisper, his breath hot against Dean’s ear. 

“ _Yes, oh God, yes_ ,” Dean moaned, desire starting to bubble up in the pit of his stomach once more. 

“Good boy,” Castiel praised, gently running his fingertips down the length of Dean’s exposed thigh. “Now, get up and put your clothes back on.” 

“B-but sir,” Dean pouted, looking at Castiel as though he had slapped him. 

“What did I tell you about whining, Mr. Winchester?” Castiel inquired in a sharp tone, narrowing his eyes at the younger man. 

“…You don’t like it…Sorry sir,” Dean sighed as he reluctantly stood up. 

Making a tsk noise, Castiel gave the younger man a thorough once over as he made his way around the desk to grab his clothes. 

“You’re going to be a handful, Mr. Winchester, I can already tell. Not to worry though, I’m more than happy to fuck you into submission,” Castiel stated, eliciting an animalistic moan from Dean. 

“…And I’d be more than happy to see you try, _sir_ ,” Dean managed to retort, although his body was trembling. 

“Indeed, let the games begin,” Castiel replied coolly and it was then that Dean knew he was so utterly screwed...in the best possible way of course.


	14. Chapter 14

**Notes for the Chapter:**

> Prompt: 14. 69
> 
> I'm so sorry this has turned into a "when I get around to it" challenge rather than a 30 day one. D: Good news is, I am done with college! So hopefully I will be able to update more frequently. Lol 
> 
> Enjoy!

Lying in bed with his nose buried in a mystery novel, Castiel didn’t even bother to look up from his reading when he heard his husband emerge from the bathroom into the guest bedroom they were staying in. 

“Your parents stocked their guest bathroom with vanilla scented shampoo, Cas. Vanilla!” Dean griped, a large, fluffy white towel wrapped around his waist as he made his way over to sit next to Castiel on the bed. 

“What’s wrong with vanilla? Don’t you like the smell?” Castiel asked halfheartedly, still trying to concentrate on his book. 

“…Yeah, but c’mon baby. Men shouldn’t smell like vanilla,” Dean huffed, his sexist comment finally catching Castiel attention. 

“Really?” Castiel questioned as he marked his place in order to set the paperback book he was reading on the table beside the bed. “What about my shampoo at home? I enjoy my hair smelling like green apple, does that make me any less of a man? Or is vanilla the only scent you associate with being a woman? Wait, let me guess? Men should only smell like sweat, dirt and testosterone, right?” 

“…Shit…I’m sorry baby…I didn’t mean to offend you,” Dean apologized, lowering his head in shame. 

“…It’s okay Dean," Castiel sighed, shaking his head. "You just have to think before you let sexist shit like that come out of your mouth. I know you were raised by an assbutt that truly believes men are superior to women but I’m here to tell you that's complete nonsense,” he added teasingly, trying to lighten the mood. 

“I know Cas. I really put my foot in my mouth, didn’t I?” Dean asked playfully, looking up at his husband. 

“That you did, handsome,” Castiel agreed, leaning forward to give Dean a quick kiss on the lips. 

“Well, looks like I’ll just have to put something else in my mouth to make up for it,” Dean flirted, reaching over to palm at Castiel’s cock through his pajama bottoms. 

“Dean,” Castiel warned, trying to hold back a moan. “While it pains me to have to turn down a blowjob, you know I’m too… _vocal_ for us to fool around right now. My parents are asleep two doors down.”

“C’mon baby,” Dean pleaded. “Hey, I’ve got an idea. How about I put something in your mouth as well? You know, to keep you quiet?” he suggested suddenly, shooting Castiel a mischievous grin. 

“You're a filthy pervert,” Castiel grumbled when Dean got up from the bed, dropping the towel that was around his waist before making his way over to the other side of the mattress where he laid down flat on his back. 

“ _Oh please_ Cas, don’t act like you don’t want to do it," the other man taunted, watching intently as Castiel stood to remove his pajamas, pulling down his pants and boxes to reveal that he was already half hard. “Damn baby, you want me that bad?” Dean asked, smiling cockily as his husband got back on the bed and crawled toward him. 

“Hey, you might be a loud-mouth asshole, but you’re my loud-mouth asshole. And there’s no denying that you are hot as hell,” Castiel laughed, carefully putting his knees on either side of Dean’s head so that they were pushed up against the tops of his shoulders, his mouth hovering over his husband’s cock. 

“You’re pretty sexy yourself, angel,” Dean replied, letting out a sharp gasp when Castiel licked up the length of his cock before swirling his tongue around the slit, greedily lapping at the pre-cum pooled there. 

Reaching over with his right hand, Castiel then began to stroke Dean’s cock lazily, planting his other hand flat on the bed so that he could look over his shoulder, smiling at his husband like the cat that caught the canary. 

“Shouldn’t you be doing something with that mouth of yours, Mr. Winchester?” Castiel asked, his grip on Dean’s cock tightening when the man beneath him ran his tongue across his balls. 

Smirking, Dean lifted up both his hands to spread Castiel’s ass cheeks apart before circling his tongue around his entrance. 

“ _Dean_ ,” Castiel mewled, goosebumps breaking out across his skin as his husband repeated the action a couple more times. 

“Shh baby,” Dean whispered, squeezing Castiel’s ass cheeks lightly. 

Taking the hint, Castiel returned to his previous task and took Dean in his mouth, massaging his tongue along the shaft of his cock. 

Trying to muffle a needy whimper, Dean followed suit and began to bob his head, reaching up to rub Castiel’s balls with his thumb. 

Meanwhile, Castiel was sucking his dick like he was getting paid for it and more than once a wave of pleasure rolled through Dean that was so good he found himself arching his hips, moaning around his husband’s cock. 

“Shit baby, you’re so fucking good at that,” Dean purred before taking the head of Castiel’s cock in his mouth once more, teasing him by sucking at it gently. 

Castiel answered in the form of a low, prideful hum, the vibrations from it setting Dean’s skin on fire. 

Grabbing ahold of Castiel’s legs, Dean bucked his hips again, deep-throating his husband’s cock as he came hard. 

“Oh God, _Dean_ ,” Castiel whispered, finding his release seconds later. 

Licking his lips, Dean let out a little noise of satisfaction as his husband shifted positions, moving to lie next to him in the bed. 

“That was fucking awesome,” Dean mumbled, pulling Castiel over so that he was resting his head on his chest. 

“…Damn it, Winchester. We just sucked each other’s dicks in guest room of my parents' house while visiting them for Christmas…We are going to Hell,” Castiel huffed, nuzzling against his husband nevertheless. 

“At least we’re going together?” Dean chuckled, earning one of the most masterful bitchfaces his husband had ever mustered.

**Author's Note:**

> Hehe I couldn't resist. ;P
> 
> (P.S. I will add more appropriate tags as I go along.) And I humbly ask for blanket forgiveness for any spelling or grammar errors made over the course of this challenge. <3 Thanks and enjoy!


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